Over the course of a half-century, the Draper family has carved out a name (and a fortune) in a place where breeding and ancestry are thought to be irrelevant. Now it's time for the debut of the youngest generation.

Last year, Deb Meyerson and Steve Zuckerman dropped out of successful careers and went sailing with their kids. How do you make a dream a reality? Good fortune, of course, but also resolve, discipline, and a willingness to live with uncertainty.